Stories
by HeathenVampires
Summary: Hiccup is an evil overlord with a willing (and eager) harem of servants and submissives, people who lean to his power, his charisma, and the fact that he has some of the best health benefits any evil overlord has ever offered. Includes, aside from Valcup... Astrid/Heather/Ruffnut/Mala/Atali/Cami/Minden/Tuffnut/Snotlout/Eret/Dagur. Supposedly crackfic. Kinktober 2018.


**OK. Number 28. Please leave sanity, judgement and any semblance of reality at the door, and buckle in for the crackfest of Kinktober.**

 **At least, that's the plan.**

 **I can't call it a ship, precisely, but characters of the day include Hiccup/Valka/Astrid/Heather/Ruffnut/Mala/Atali/Cami/Minden/Tuffnut/Snotlout/Eret/Dagur... I think that's everyone. And I don't just mean everyone in the fandom haha. Also yes beware incest themes. As in, Hiccup and Valka explicitly fuck, just so you know.**

 **Kinks include, but may not be limited to... collaring, incest, begging, sixty-nine, dirty talk, master/slave, exhibitionism, voyeurism, breast worship, cock worship, biting, praise kink, body worship, strip-tease, masturbation, seduction. And idk, I guess Dom/sub but that might come under master/slave. The point is the prompter took a look at the kinktober list and went "one of each please" and I went "yes, let's do this" like the smuttiest pick and mix counter there ever was.**

 **And... here we go! Hopefully. Or perhaps farewell forever. Could just be a major disappointment. This is the longest authors note in the world I am rambling someone stop me.**

-HTTYD-

As an evil overlord, Hiccup had to strive to attract the true loyalty of his followers. Mostly, he thought it was the health plan they got that brought them in. What kept them in? Well... he took care of quite a few of them in other ways too. Perhaps slightly less practical than with health insurance, but many times more satisfying.

"Are we done talking for the day? I have things to be doing and it sounds like my personal empire is doing just fine."

Viggo, his mentor of sorts who helped keep an eye on things while Hiccup was... busy, huffed, but he knew full well what other things Hiccup had to be getting to, and he was not the type to dare interfere with that. Standing up from where they were sat, a functional table full of papers, they tidied up the paperwork into its piles - who knew running an evil empire involved so much admin? - and Viggo let Hiccup walk him out.

"Enjoy your evening Hiccup."

"Oh I will."

Waving off his mentor, Hiccup adjusted his very evil cape, swooshing it behind him as he headed back through his domain, a personal headquarters where Hiccup conducted business in one half, and the other was entirely dedicated to the conduct of pleasure. Only his... Hiccup supposed the word 'harem' applied, though if he could find another word to describe the group of willing and eager sub-or-switch types he had seduced over the acquisitions of his evil empire, he'd use it. It only took a few steps into the room before several of them looked up, having clearly been waiting for Hiccup to arrive. They swarmed him, respectfully, awaiting their orders as Hiccup headed to his throne and settled himself comfortably.

"Entertain me."

There was little preamble before three of his switch-types had their first idea on how to entertain Hiccup, Mala, Minden and Atali all removing what few clothes they had on before drawing each other close. Hiccup cocked his head, watching the way hands roamed skin, knowing and practiced, hungry moans filling the space between kisses. The thing he loved about those three in particular playing together was that there was no fakery; they knew Hiccup wanted to see real, genuine pleasure. And oh, they knew how to do that. Mala's mouth roved Atali's neck, sliding down to her collarbone as hands played over her curves, the trio kissing, stroking, gasping wetly in muted enjoyment as arousal built slow and steady.

Minden was first to lower herself - literally, lowering herself until her mouth was what made Mala arch and buck, long fingers slipping into dark and strawberry-blonde hair alike as Atali's lips reached Mala's breast. Everyone else had sort of... stopped, watching right along with him for the moment as limbs twined, tumbling down to the ground to taste and caress each other. Hiccup rested his chin on one hand, feeling the early stirrings in his groin and letting the other hand trail down, combing through her hair where she sat next to his chair, all but purring.

No longer content with not being in Hiccup's line of attention, he watched as first Ruff, then Astrid and Heather got up, each taking turns to seduce him slowly with a sensual strip-tease. Heather wore more layers, but no underwear, so as her undershirt hit the floor Hiccup watched her cup and toy with her own breast. Astrid tossed her bra toward Hiccup as she shed it, inviting him to look over to her. If there was ever a time to enjoy the tough choice of where to look as Ruff kicked off her skirt, it was now. Hiccup leant back into his throne properly, allowing him to keep all three women in his eyeline.

When the men started joining in - he appreciated many forms of entertainment, particularly when it came to the human form - Hiccup struggled a little more to keep them all in centre stage. Tuff started it, not wanting to be outdone in the strip-show by his twin sister. Naturally, Scott could not be left behind, and he soon began to shed his own attire, tossing top and bottoms haphazardly aside... there was going to be one hel of a clean up needed later, but that was nothing new. Waiting until he could be the only one undressing, Dagur flexed and stretched in his best attempt at sexy, which was actually pretty good, surprisingly fluid hips undulating as the redhead pushed down his bottoms.

"It woulda been better with music, but then we couldn't hear them!"

Dagur gestured to where Mala and Atali were on their sides, both rather eagerly going down on the other with groping hands and stifled moans, capturing everyones attention for the moment before the atmosphere began to affect everybody else. Hiccup squeezed his erection through his bottoms, nodding to the others to go on as they wished. Astrid reached for Dagur, dragging him to the floor to clamber on top of him, eager fingers curling around a semi-hard cock while others nudged and pressed between quivering thighs, arousing the other in preparation, stoking the low embers into a pleasant, warming fire.

Equally as... flexible with their lovers as Hiccup was, the others had not restricted themselves to heterosexual encounters either. Ruff and Heather were quite happily entangled, slender limbs and demanding hands twisting, touching, groping. Scott and Tuff were equally as close, rutting and growling and undoubtedly going to make a big mess on Hiccup's floor. Not that he minded terribly. That happened a lot.

Each of the pairs were keeping an eye on Hiccup though, wanting to be the ones to seduce him that evening, to tempt him to join them and satisfy them in his creative, unique way. Hiccup indulged himself in each of them quite regularly, but none ever seemed to quite get enough, and everyone knew he had a favourite.

Hiccup soon realised where Minden had gone, no longer part of the enthusiastic actions between Mala and Atali, when she and Cami appeared much closer to him than before, interested eyes focused on his erection and pleading expressions aimed toward his face. Considering the strain of his cock, demanding something in the midst of all the sexuality filling the air around them, Hiccup wasn't want to turn them down and nodded, unbuckling his belt before sliding down his seat a little, widening his legs and waiting.

Cami's small, nimble fingers were what drew Hiccup free of his trousers, his cock pulsing against her palm as she exposed him fully, beckoning Minden over to join her. Hiccup let his head roll back for a minute, just focusing on the feeling of two tongues, two mouths, wet and sloppy as they licked and sucked him with no rhyme or reason. When he finally raised his head again, he was treated to the sight of a blonde head followed by brown, working up and down the sides of his cock before taking turns giving the head a sharp suck, mouthing over his sac and both women smirked when Hiccup groaned and bucked his hips.

"Someone wants to give you the full works boss."

Hiccup looked up, saw tall, tattooed and muscular as Eret approached, kneeling down as the women moved aside to give his heavy frame room. Eret was especially good at taking Hiccup down his throat, pulling many an explosive climax from their overlord with his obscenely talented mouth. Already sensitive with the teasing, lovely efforts of Cami and Minden, he groaned as Eret swallowed him down with ease, barely seeming to move before Hiccup felt the tight muscles of his throat squeeze around swollen shaft, wet gurgles and sloppy, messy lips accompanying that pleasurable vice.

Broad hands settled, one against his hips to stop Hiccup seeking more, to make him take only what Eret offered. Of all his submissives, Eret was by far the cheekiest, though he more often than not was doing it so Hiccup would be rougher with him in 'punishment'. Hiccup wondered briefly how much of a punishment it was when Eret enjoyed it quite so much. Then Eret swallowed again, and the sinfully tight grip around his shaft blanked Hiccup's mind of much beyond bliss, knowing it wouldn't take much more for Eret to have Hiccup spill down his throat.

Hiccup felt a hand on his knee, looked to see wide green eyes watching Eret work, closing in pleasure when he carded somewhat uncooperative fingers through her soft hair. Those same fingers tightened as Eret finally got Hiccup to the edge, another tight swallow enough to have him over it, shuddering with a low groan as Eret took it all, sitting back on his haunches with flushed cheeks and swollen lips, wiping at his wet chin while still grinning rather smugly.

"Show off."

Cami jibed, pulling faces at Eret before she pounced at Minden for her own... entertainment. Fixing his trousers for the moment, Hiccup stretched his arms before turning to where his mother waited, eyes wide as Hiccup picked something up and beckoned her to rise to his level. Gods, she was so beautiful, tall and lithe with that gorgeous long hair fallen down to her waist. She moved, taking Hiccup's kiss eagerly, mewling in disappointment when he stopped. Hiccup smirked, stroking her jaw before turning her head slightly.

"Here we go" the collar was custom made for her, a gift, one she'd wear more often if it didn't so clearly claim his mother as his, something that not everybody beyond the walls around them should be privy to "that's better isn't it?"

Valka nodded, letting Hiccup seat her in his lap, tugging the offending tie of her gown open to expose the bare body beneath. He took her in with eyes first, breathless with the perfect woman who both birthed him and fucked him. Running one finger down between her breasts, Hiccup smiled as she squirmed, a faint flush of arousal already tinging her skin pink and breath coming in deep pants. It was amusing, almost, to reconcile the two in his mind - the fierce, feral woman outside of sex, and the soft, tender submissive she became during. But Hiccup knew it was her gift to him, something they both thrilled in - almost an apology for not being there when he was a boy, though Hiccup had ascertained that Valka still actively wanted him first. He'd never forgive himself for making his mother do things she didn't want to, that she just thought she had to.

Instead, he simply had a pliant goddess in his hold, letting out soft and sinful sounds as Hiccup explored her more thoroughly. Soft breasts, warm and yielding to the touch. The angle made it a little difficult to use both hands on her, and right now Hiccup decided that would not do.

"Lie down for me?"

Valka obeyed immediately, perfectly, only peering up for Hiccup to tell her to lie on her back or front. Hiccup drew Eret over, feeling playful as he had the other man hold his mothers hands down. She shivered under his hands as Hiccup stroked her skin, tracing the lines of lean muscles in her thighs, strong and agile. He could adore her body for days and never get bored of the patterns of old scars, faded stretchmarks, the little dimples in her lower back, the soft curve of her hips. Hiccup moved up to kiss her lips, seeing that haze of love and lust in her big green eyes, pressed a kiss to the streaks of silver-grey along her hairline.

"Beautiful. You're so perfect, so good for me."

He hooked a finger under her collar, used it to pull Valka up enough that he could kiss her again, biting playfully at her lips as she moaned weakly, the already tight collar pressing against her throat with him tugging it.

"Hiccup... please... son..."

Oh, the minx knew how to get to him all the same. Hiccup often felt that despite her submission, his mother was very much the one in control. She knew all his buttons, the right way to push to get exactly what she wanted. Hiccup felt his cock stir again, not quite yet ready to give in to her yet though as he trailed a finger over her soft belly, reaching up with one hand to thumb her straining, neglected nipple, loving the way she bucked and moaned aloud. They had everyone elses attention by now, some still fucking but everybody watching Hiccup and his personal favourite.

Pleading, Valka fixed him with those _eyes_ again, bright and green and hungry for him as her hands strained against Eret's hold.

"Don't let her go now. You know how she misbehaves."

"You got it boss."

Hiccup chuckled as his mother whined, kneeling between her spread legs to stretch up and suckle her breast, flicking his tongue against her nipple as his fingers slipped down, a hungry sound rumbling in his own chest as he felt how hot she was, wet enough to make his fingers slip in her slickness as he circled them around her clit.

Already sensitive as she was, Valka pitched, pushing her hips up and against his hand, fighting harder against Eret's restraining of her to try and grab his head, hold Hiccup to her chest so his mouth would continue tormenting her nipple. Hiccup lifted his mouth free, watching the way her face betrayed disappointment and pleasure in equal mix, his fingers still busy against that swollen little bud.

"Maybe I'm not enough for you tonight, you seem especially desperate. Shall I have some of the others come play too?"

Torn, Valka ended up nodding, seeming finally somewhat content as several hands and mouths found their way over her skin. Hiccup stood back for a minute, simply watching as his mother took her first climax of the evening. First of many, usually. Hiccup liked to keep her satisfied. His mothers cries drowned out almost any other sound, each exquisite moan and curse going straight to Hiccup's cock, demanding to be within the silken heat he knew he would find inside Valka.

Nudging a few of them out of his way, Hiccup knelt down and lowered his mouth, knowing she'd be too sensitive and enjoying the frantic sounds a little too much as he tasted musk and sin, licking his lips eagerly as he reared back, hands at his belt again.

"Is this what you want mom?"

"Yes! Please Hiccup, I need you!"

When she put it like that, it seemed rude to deny his mother any further. Hiccup wasted little time in pulling her hips up into his lap, guiding his swollen cock inside her and feeling soft and wet admit him easily. Valka was still held down, unable to really move much in the position her son had drawn her in to. Hiccup was happy to do the work for her right now.

Not quite come down from the previous climax yet, Hiccup felt her begin to approach a second almost as soon as he started thrusting, stroking his cock up over her g-spot and ensuring he settled deep within each time, letting her feel him properly.

Many eyes were on them, several people touching themselves or each other as the erotic display unfolded before them. His mother seized, swore under her breath as those rhythmic spasms told Hiccup she'd climaxed again. It wasn't the explosive type he was aiming for though, wanting to leave his mother a trembling wreck.

Nodding to Eret to let her go, Hiccup almost fell back with the surging of Valka coming up to grab him, hauling him into a biting kiss, rutting her hips to ride him urgently, needing more. Fingers scratched his scalp as she clutched him, whining in complaint when her attempts to touch him properly were impeded by his jumper and very evil cloak.

Since they were both close by, Hiccup brought Eret and Dagur in to join the party, letting his mother rest against his chest while Eret lubed himself up, worked slick fingers into her cute little ass. Hiccup groaned in sync with her as Eret pushed in, feeling the drag of his cock close by, feeling the tremors in Valka's muscles from being so very full. Still not content, she reached for Dagur, uncaring - or happy, Hel, his mother was kinky like that - that his cock was still wet with Astrid, letting the muscular red-head pump his cock into her mouth.

How she had that much concentration, Hiccup had no idea. On the rare times he was in the mood to be fucked himself, two people was his limit for focus. There went his mother, working three men at once and, judging by the way she began to tighten around him again, enjoying every minute. Eret groped her chest from behind, big hands squeezing and pinching harshly, leaving Hiccup free to reach down and toy with her clit, cock clenched in her heat as she came yet again, shaking and trembling between the three of them as everybody watched on…

* * *

"And that, mom, is what it would be like if I was an evil overlord."

Lifting up to rest his head on his arm, Hiccup watched his mother look at him in utter bemusement.

"I think you've been reading too many stories son."

Chuckling, he pulled her into a kiss.

"You made me love stories to begin with. So it's your fault."

"I am totally certain I never told you stories like that."

"Yes, well, now you make me think a lot of naughty things before bed. Same thing really. You always did have that effect on me. And you're missing the moral of the story."

Blinking, Valka shook her head, reaching to stroke his hair and smiling when Hiccup turned to plant a kiss on his mothers wrist.

"There was a moral in there somewhere?"

"Yep. No matter what, you'll always be my favourite."

-HTTYD-

 **Oh boy. This didn't turn out how I expected at all. I don't know if it counts as crackfic anymore. I tried ok? Kinktober has been one very long month, not least because we're almost halfway into November now! Oh well. I did a thing. It was fun. Hopefully FF stops having errors long enough for me to upload it.**


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